Kara Swisher on Ambition, Bragging, and Having a Baby at 56

Kara Swisher. Photo-Illustration: by Stevie Remsberg; Photos: Getty

Doing the Most is a special series about ambition — how we define it, harness it, and conquer it. As part of the theme, we’re interviewing successful women about what makes them so good at what they do.

Arguably the most feared and respected tech journalist in the business, Kara Swisher is such a household name that she played herself on HBO’s Silicon Valley. (She’s also one of the only reporters who can make Mark Zuckerberg sweat through his hoodie.) She began covering tech in the early ’90s and later co-founded the news website Recode, which was acquired by Vox in 2015. Now, she writes a weekly column for the New York Times, produces two podcasts for Vox, appears regularly on CNBC, and hosts tech-world bigwigs at her Code Conference series. We spoke to her about being the best in her field, running for mayor of San Francisco, and having a baby at 56.

When did you know that you were more ambitious than most people?
From the beginning. Like, when I was very young. My mom always tells this story: I was in second or third grade, and I walked out of the classroom. I was like, “I know this already. You’re wasting my time.” I definitely remember being bored in school and wishing things would go at a faster pace.

What kind of reaction did that get?
Oh, people would say, “Isn’t that cute.” Or, “Aren’t you bossy,” or any of the words they use for women who say what they want. I always said what I wanted from the beginning, and that continued throughout my career. There have been a lot of people, mostly men in positions of power, telling me I had to wait, that I shouldn’t be so confident. And I was like, “What are you talking about? I’m the best you have.”

I was very declarative of my qualities. And I don’t think I was being braggy. I won the journalism award in college when I was a freshman, and it was a senior award. I got a lot of pushback for it, which was weird. I was like, “Well, too bad, I beat you.” I don’t care much for awards, though. I knew I was good already. I wasn’t particularly competitive in sports, which is interesting. I didn’t want to win in games, just work.

How did you figure out where to focus your ambitions?
Originally, I wanted to be an architect. But then, in high school, I went to a summer program at Harvard for architecture, and I was just bad. I don’t have talent in design. I wish I could do it, but I didn’t pursue it because I knew I wasn’t going to be the best.

I also wanted to go into the military, maybe to be in the CIA, and I couldn’t because I was gay. That was more a function of the time. If I wasn’t gay, I probably would’ve become a spy. I think I would have been good at it. When they got rid of “Don’t ask, don’t tell,” I thought about joining the Reserves, but by that point I was too old.

So you went into journalism. Did you get a lot of pushback from your bosses when you were young?
I got an internship at the Washington Post in my junior year of college. I was like, “You should hire me because I’m better than the other people you have.” And I kept saying that pretty much at every juncture of my career. I knew I was a good communicator and a good writer, and I wasn’t shy. I think most people do know when they’re good at things, and they do know their value, but then other people chip away at it. I don’t have impostor syndrome.

A lot of people have said to me, “You should be more humble.” And I’m like, “Why?” Bragging is different than saying what it is. When I suck at something, I say I suck at it. But I know what I’m good at.

Where do you think you got your “world is my oyster” mentality? Can you attribute it to anything?
I love oysters, by the way. They’re my favorite food. But anyway, I always knew I was lucky. I grew up in a wealthy environment. I have a lot of advantages. So I don’t spend a lot of time thinking about the struggles I have because I know that I am very lucky in lots of ways.

Also, I’ve never worried about what people thought of me, and I think part of that had to do with being gay. My feeling at the time was, Well, if they don’t like me because I’m gay, what’s the difference? I think it frees you. If people don’t like you for some inane reason, then why worry what they think? And if you don’t worry about what people think of you, you can do almost anything.

My dad died when I was 5. I remember thinking, The worst thing ever happened to me and I’m still here. Being aware of death tends to clear out the brush. Anytime I’m having a minute, I remember, Oh, I’ll be dead in 50 years. Okay. And then I stand up. I’m not death-obsessed, but I’m death-aware. It keeps me focused.

You’ve had some notoriously bad bosses. How did you cope with them?
I’ve definitely been in abusive workplaces. But there are also types of bosses who try to hold you back a little bit, in small ways. I had one boss who, when I came back from maternity leave, said, “I guess you’ll need more time now.” And I was like, “For what? It’s not because I had a baby, right? Because it would be wrong for you to say that.” He was so awkward. I said, “I was the best before and I’m still going to be the best.” A lot of people would have let that kind of comment go, but I often say out loud what people are thinking. And in that case, there wasn’t any cost to me because I really was good.

Do you have high standards outside of work too? How does it affect your relationships?
I don’t know that I’m ambitious in other parts of my life. I don’t push my kids that much, especially compared to other parents. I have two wonderful boys, and I spend a lot of time with them. I’m always like, “Don’t do your homework; it doesn’t matter. Do this other thing instead.” Their teachers hate me for it, but I’m like, “What? Is it not true?” We try to help our kids with what they want to do, but you’re certainly not going to see me bribing any colleges. We’re much more hands off than you might imagine. I don’t think I’m particularly ambitious with my love life either. I was married for a long time, but then … Well, I’m having a baby in November with my girlfriend, so I guess that’s ambitious. You probably have to be pretty ambitious to have a baby at 56. I’ve always wanted a girl, so I’m excited. [Her girlfriend is carrying.]

Has parenthood affected your ambitions at all?
Becoming a parent didn’t lessen my ambition, but it did make me more sanguine about work. It makes me spend even less time worrying about what people think of me. When something bad happens at work, or someone gives me a hard time, I’m like, “I don’t need you to like me. I have dogs. I have kids. I need them to like me.” If I fail at being a parent, I feel terrible, but if I fail at some work thing, I’m like, Oh, well. Not everything’s a four-alarm fire. If something goes wrong, a lot of people are like, “What are we going to do!?” And I’m like, “Something else.”

Does your ambition ebb and flow at all? 
No. I’m more ambitious now than ever. I just thought of a new idea for something, and I told my girlfriend about it, and she was like, “Really?” I already have a lot of jobs, and she makes fun of me for it. But I like creating things. I really enjoy it. I think I’m probably more entrepreneurial than most reporters. I always try to keep myself amused. Starting the podcast was part of that. A lot of people told me it wouldn’t work and I just ignored them completely.

I think I work harder than most people, certainly. Some people ask, “Why are you successful?” And I’m like, “I work harder than you.” I do have talent, but I also put in the time. I’m not embarrassed about it either, and I don’t pretend it’s not important.

When I had a stroke, everyone was like, “Oh, now you have to take time off.” But I was fine. I did a video an hour later. I’d never been sick at all, and it’s not like any stroke is good, but it was the best stroke you could have, I guess. I recovered fully and immediately. And I love my work. It’s not a choice between that and my personal life.

Do you ever get tired?
Maggie Haberman just asked me that. She was like, “Do you ever get tired?” And I was like, “No.” I just don’t. I don’t feel tired. And when I’m tired I go to sleep. I’m pretty energetic for someone my age, but I’ve always had a lot of energy, and I think I’ll be that way until I’m dead.

How do you know when you’ve taken on too much? Do you get overwhelmed?
If I can’t do something well, I drop it. I write the column every week. I do five or six podcasts a week, at least. I do CNBC once or twice a week, and then I’m working on events. But Vox lets me work from wherever I want. I can work at night and keep weird hours. I do take breaks. The other night I went to go see the new Gerard Butler movie by myself. I love all those Has Fallen movies, London Has Fallen, The White House Has Fallen. I don’t know what it is about them, but I love them. So I just went by myself. I had a million other things to do, but I just wanted to see it. Someone asked me who I was going with, and I was like, “Me.” And then I was up really late last night working on my Times article. I work when I feel like it. Some mornings I take off, some mornings I don’t. I calibrate my own schedule. There’s no nine-to-five hours in my life. I’m super anal-retentive, so I make lists and I’m very organized.

Also, I say no a lot. Like, “I won’t do that. No, I don’t want that.” Women are made to feel that they should be a good girl or be accommodating, and they suffer for that. It’s a societal thing. And men get to sit back and say no. The ability to say no is, I think, the greatest power of all time. And then saying yes at the right time, too.

You’ve talked about running for mayor of San Francisco. Is that still something you want to do?
Yes, I still think about it all the time. But we just got a new mayor, and I want to give her a chance. I don’t want to step on her toes and be that asshole who just runs for personal ambition. Also, I’m having a baby now, so I’ll be on the East Coast more. I don’t know. We’ll see. I do want to run for public office at some point. I’ve just got to figure out when I can do it. Maybe when I’m 70.

How do you celebrate your successes? Do you ever take a moment just to bask in it?
I don’t spend a lot of time high-fiving, just like I don’t spend a lot of time agonizing when something goes wrong. I play the long game. I always say that to people when they’re panicking. People are so panicked. I did Outward Bound twice, when I was 19 and 25, and the people who did well on Outward Bound were the ones who weren’t panicking. There’s sometimes reason to be worried, but most of the times people just panic instead. I’m a super calm person, both when things are going well and when things are going badly. Of all the skills I have, my ability to move on is one of the keys to my success. I’m like, “Next!” So I never feel defeated, in the same way that I never feel victorious.

This interview has been condensed and edited.

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Kara Swisher on Ambition, Bragging, and Having a Baby at 56